Etymology
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cross (v.)

c. 1200, "make the sign of a cross as an act of devotion," from cross (n.) and in part from French croiser. Sense of "to go across, pass from side to side of, pass over" is from c. 1400; that of "to cancel by drawing a line over or crossed lines over" is from mid-15c.

From late 14c. as "lie across; intersect;" also "place (two things) crosswise of each other; lay one thing across another." From early 15c. as "mark a cross on." Meaning "thwart, obstruct, hinder, oppose" is from 1550s. Meaning "to draw or run a line athwart or across" is from 1703. Also in Middle English in now-archaic sense "crucify" (mid-14c.), hence, figuratively, crossed "carrying a cross of affliction or penance."

Sense of "cause to interbreed" is from 1754. In telegraphy, electricity, etc., in reference to accidental contact of two wires on different circuits or different parts of a circuit that allows part of the current to flow from one to the other, from 1884. Meaning "to cheat" is by 1823.

Cross my heart as a vow is from 1898. To cross over as euphemistic for "to die" is from 1930. To cross (someone's) path "thwart, obstruct, oppose" is from 1818. Of ideas, etc., to cross (someone's) mind "enter into" (of an idea, etc.) is from 1768; the notion is of something entering the mind as if passing athwart it.

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live (v.)

Middle English liven, from Old English lifian (Anglian), libban (West Saxon) "to be, be alive, have life; continue in life; to experience," also "to supply oneself with food, procure a means of subsistence; pass life in a specified fashion," from Proto-Germanic *libejanan (source also of Old Norse lifa "to be left; to live; to live on," of fire, "to burn;" Old Frisian libba, German leben, Gothic liban "to live"), from PIE root *leip- "to stick, adhere," forming words meaning "to remain, continue."

Meaning "to make a residence, dwell" is from c. 1200. Meaning "express in one's life" (live a lie) is from 1540s. Intensified sense "have life abundantly, make full use of life's opportunities" is from c. 1600. Related: Lived; living.

To live it up "live gaily and extravagantly" is from 1903. To live up to "act in accordance with, not live below the standard of" is 1690s, from earlier live up "live on a high (moral or mental) level" (1680s). To live (something) down "cause (something disreputable) to be forgotten by subsequent blameless course, live so as to disprove" is from 1842. To live with "cohabit as husband and wife" is attested from 1749; sense of "to put up with" is attested from 1937. Expression live and learn is attested from c. 1620.

According to the Dutch Prouerbe ... Leuen ende laetan leuen, To liue and to let others liue. [Gerard de Malynes, 1622]
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road (n.)

Middle English rode, from Old English rad "riding expedition, journey, hostile incursion," from Proto-Germanic *raido (source also of Old Frisian red "ride," Old Saxon reda, Middle Dutch rede, Old High German reita "foray, raid"), from PIE *reidh- "to ride" (see ride (v.)). Also related to raid (n.).

In Middle English it was still, "a riding, a journey on horseback; a mounted raid;" the sense of "an open passage or way for traveling between two places" is recorded from 1590s, and the older senses now are obsolete. "The late appearance of this sense makes its development from sense 1 somewhat obscure," according to OED, which however finds similar evolutions in Flemish and Frisian words. The modern spelling was established 18c.  

The meaning "narrow stretch of sheltered water near shore where ships can lie at anchor" is from early 14c. (as in Virginia's Hampton Roads). In late 19c. U.S. use it is often short for railroad.

On the road "traveling" is from 1640s. Road test (n.) of a vehicle's performance is by 1906; as a verb from 1937. Road hog "one who is objectionable on the road" [OED] is attested from 1886; road rage is by 1988. Road map is from 1786; road trip is by 1950, originally of baseball teams. Old English had radwerig "weary of traveling."

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sleep (v.)

Middle English slepen, from Old English slæpan "to be or fall asleep; lie or remain dormant or inactive" (class VII strong verb; past tense slep, past participle slæpen), from Proto-Germanic *slēpanan (source also of Old Saxon slapan, Old Frisian slepa, Middle Dutch slapen, Dutch slapen, Old High German slafen, German schlafen, Gothic slepan "to sleep"), from PIE *sleb- "to be weak, sleep," which perhaps is connected to root *sleg- "be slack, be languid," the source of slack (adj.). Sleep with "do the sex act with" is in Old English:

Gif hwa fæmnan beswice unbeweddode, and hire mid slæpe ... [Laws of King Alfred, c. 900]

Related: Slept; sleeping. There is no cognate form of the verb in Scandinavian. The usual PIE root is *swep-. The meaning "to rest as in the grave" is from Old English. In reference to parts of the body, "be numb through stoppage of circulation," late Old English. The sense of "provide or afford sleeping accommodations for" is by 1848, American English.

To sleep in "remain in bed in the morning" is by 1827; to sleep out "spend the night in the open" is by 1852. To sleep (something) off "remove the effects of by sleeping" is from 1760 (sleep out in the same sense is from 1550s). To sleep on some matter "postpone decision until the following day" is from 1510s, perhaps suggesting guidance in a dream. To sleep around "have casual sex with multiple partners" is attested by 1928.

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un- (1)

prefix of negation, Old English un-, from Proto-Germanic *un- (source also of Old Saxon, Old Frisian, Old High German, German un-, Gothic un-, Dutch on-), from PIE *n- (source of Sanskrit a-, an- "not," Greek a-, an-, Old Irish an-, Latin in-), combining form of PIE root *ne- "not." Often euphemistic (such as untruth for "lie").

The most prolific of English prefixes, freely and widely used in Old English, where it forms more than 1,000 compounds. It underwent a mass extinction in early Middle English, but emerged with renewed vigor 16c. to form compounds with native and imported words. It disputes with Latin-derived cognate in- (1) the right to form the negation of certain words (indigestable/undigestable, etc.), and though both might be deployed in cooperation to indicate shades of meaning (unfamous/infamous), typically they are not.

It also makes words from phrases (such as uncalled-for, c. 1600; undreamed-of, 1630s; uncome-at-able, 1690s; unputdownable, 1947, of a book; un-in-one-breath-utterable, Ben Jonson; etc., but the habit is not restricted to un-; such as put-up-able-with, 1812). As a prefix in telegramese to replace not and save the cost of a word, it is attested by 1936.

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by (prep., adv.)

Old English be- (unstressed) or bi (stressed) "near, in, by, during, about," from Proto-Germanic *bi "around, about," in compounds often merely intensive (source also of Old Saxon and Old Frisian bi "by, near," Middle Dutch bie, Dutch bij, German bei "by, at, near," Gothic bi "about"), from PIE *bhi, reduced form of root *ambhi- "around."

As an adverb by c. 1300, "near, close at hand."

OED (2nd ed. print) has 38 distinct definitions of it as a preposition. Originally an adverbial particle of place, which sense survives in place names (Whitby, Grimsby, etc., also compare rudesby). Elliptical use for "secondary course" was in Old English (opposed to main, as in byway, also compare by-blow "illegitimate child," 1590s, Middle English loteby "a concubine," from obsolete lote "to lurk, lie hidden"). This also is the sense of the second by in the phrase by the by (1610s).

By the way literally means "along the way" (c. 1200), hence "in passing by," used figuratively to introduce a tangential observation ("incidentally") by 1540s. To swear by something or someone is in Old English, perhaps originally "in the presence of." Phrase by and by (early 14c.) originally meant "one by one," with by apparently denoting succession; modern sense of "before long" is from 1520s.

By and large "in all its length and breadth" (1660s) originally was nautical, "sailing to the wind and off it," hence "in one direction then another;" from nautical expression large wind, one that crosses the ship's line in a favorable direction.

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sit (v.)

"To be or remain in that posture in which the weight of the body rests upon the posteriors" [OED], Middle English sitten, from Old English sittan "occupy a seat, be seated, sit down, seat oneself; remain, continue; settle, encamp; lie in wait; besiege" (class V strong verb; past tense sæt, past participle seten), from Proto-Germanic *setjan (source also of Old Saxon sittian, Old Norse sitja, Danish sidde, Old Frisian sitta, Middle Dutch sitten, Dutch zitten, Old High German sizzan, German sitzen, Gothic sitan), from PIE root *sed- (1) "to sit."

With past tense sat (formerly also set, which is now restricted to dialect, and sate, now archaic); and past participle sat, formerly sitten. The meaning "to have a seat in a legislative assembly" is from late 14c.; in reference to the assembly, "to hold a session," from 1510s. The sense of "pose" for a portrait, etc., is by 1530s.

As short for babysit (v.) by 1966. The specific sense of "occupy a judicial seat" (Old English) is the notion in sit in judgement. The meaning "have a certain position or direction" is from c. 1200; of winds, "to blow from" (a certain quarter), 1590s, from the notion of "to be in."

To sit back "be inactive" is from 1943. To sit on one's hands originally was "withhold applause" (1926), later generalized to "do nothing" (by 1959). To sit around "be idle, do nothing" is by 1915, American English. To sit out "not take part, make oneself an exception" is from 1650s.

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melancholy (n.)

c. 1300, melancolie, malencolie, "mental disorder characterized by sullenness, gloom, irritability, and propensity to causeless and violent anger," from Old French melancolie "black bile; ill disposition, anger, annoyance" (13c.), from Late Latin melancholia, from Greek melankholia "sadness," literally (excess of) "black bile," from melas (genitive melanos) "black" (see melano-) + khole "bile" (see cholera).

Old medicine attributed mental depression to unnatural or excess "black bile," a secretion of the spleen and one of the body's four "humors," which help form and nourish the body unless altered or present in excessive amounts. The word also was used in Middle English for "sorrow, gloom" (brought on by love, disappointment, etc.), by mid-14c. As belief in the old physiology of humors faded out in the 18c. the word remained with a sense of "a gloomy state of mind," particularly when habitual or prolonged.

The Latin word also is the source of Spanish melancolia, Italian melancolia, German Melancholie, Danish melankoli, etc. Old French variant malencolie (also in Middle English) is by false association with mal "sickness."

When I go musing all alone,
Thinking of divers things fore-known,
When I build castles in the air,
Void of sorrow and void of fear,
Pleasing myself with phantasms sweet,
Methinks the time runs very fleet.
   All my joys to this are folly,
   Naught so sweet as melancholy.
When I lie waking all alone,
Recounting what I have ill done,
My thoughts on me then tyrannise,
Fear and sorrow me surprise,
Whether I tarry still or go,
Methinks the time moves very slow.
   All my griefs to this are jolly,
   Naught so sad as melancholy.
[Robert Burton, from "Anatomy of Melancholy," 17c.]
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city (n.)

c. 1200, from Old French cite "town, city" (10c., Modern French cité), from earlier citet, from Latin civitatem (nominative civitas; in Late Latin sometimes citatem) originally "citizenship, condition or rights of a citizen, membership in the community," later "community of citizens, state, commonwealth" (used, for instance of the Gaulish tribes), from civis "townsman," from PIE root *kei- (1) "to lie," also forming words for "bed, couch," and with a secondary sense of "beloved, dear."

Now "a large and important town," but originally in early Middle English a walled town, a capital or cathedral town. Distinction from town is early 14c. OED calls it "Not a native designation, but app[arently] at first a somewhat grandiose title, used instead of the OE. burh"(see borough).

Between Latin and English the sense was transferred from the inhabitants to the place. The Latin word for "city" was urbs, but a resident was civis. Civitas seems to have replaced urbs as Rome (the ultimate urbs) lost its prestige. Loss of Latin -v- is regular in French in some situations (compare alleger from alleviare; neige from nivea; jeune from juvenis. A different sound evolution from the Latin word yielded Italian citta, Catalan ciutat, Spanish ciudad, Portuguese cidade.

London is the city from 1550s. As an adjective, "pertaining to a city, urban," from c. 1300. City hall "chief municipal offices" is first recorded 1670s; to fight city hall is 1913, American English. City slicker "a smart and plausible rogue, of a kind usu. found in cities" [OED] is first recorded 1916 (see slick (adj.)). City limits is from 1825.

The newspaper city-editor, who superintends the collection and publication of local news, is from 1834, American English; hence city desk attested from 1878. Inner city first attested 1968.

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